Phosphorus pentachloride → (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1088245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088245
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.Cl.[NH2:35][C:36]1[S:40][N:39]=[C:38](/[C:41](=[N:45]/[O:46][CH3:47])/[C:42](Cl)=[O:43])[N:37]=1.P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl>[NH2:35][C:36]1[S:40][N:39]=[C:38](/[C:41](=[N:45]/[O:46][CH3:47])/[C:42]([NH:1][C@@H:2]2[C:20](=[O:21])[N:4]3[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]23)=[O:43])[N:37]=1

Komponenten

6

Edukt 4

HCID 24819Phosphorus pentachlorideHCID 11708267BistrimethylsilylacetamidHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 19930550(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl chloride;hydrochloride

Produkt 1

HCID 88417261(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 240 ml of dichloromethane is suspended 9.06 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid. To the suspension is added 28.9 g of bistrimethylsilylacetamide and the mixture is stirred at room temperature until complete dissolution and cooled in an ice-water bath. To this solution, 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacetyl chloride hydrochloride prepared from 5.83 g of 2-(5-amino-1,2,4-thiadiazol-3yl)-2(Z)-methoximinoacetic acid and 6.02 g of phosphorus pentachloride in 90 ml of dischloromelthane is added and the mixture is stirred for a while. The whole mixture is stirred with ice-cooling for 60 minutes. The dichloromethane is evaporated off and the residue is dissolved in melthyl ethyl ketone. The solution is washed with water and dried. The solvent is then evaporated off and diethyl ether is added to the residue to give a fine precipiate, which is collected by filtration, giving 11.8 (82% yield) g of the title compound.

Aufarbeitung

  1. temperaturecooled in an ice-water bath
  2. additionis added
  3. stirringthe mixture is stirred for a while
  4. stirringThe whole mixture is stirred with ice-
  5. temperaturecooling for 60 minutes
  6. customThe dichloromethane is evaporated off
  7. dissolutionthe residue is dissolved in melthyl ethyl ketone
  8. washThe solution is washed with water
  9. customdried
  10. customThe solvent is then evaporated off
  11. additiondiethyl ether is added to the residue
  12. customto give a fine precipiate, which
  13. filtrationis collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e3e14803eedf444bb42ce50a25a4151d
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04962100

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